Heeled footwear, such as boots, are worn for a variety of applications, including as Western (cowboy) boots, riding (equestrian) boots, work boots, and hiking boots. In many examples, the heel portion of an article of footwear is the first point of contact between the footwear and the ground, such that mechanical energy is transmitted into the heel region of the footwear and into the heel of the individual wearing the footwear each time the heel of the footwear strikes the ground or other solid surface. This mechanical energy further may be transferred through the wearer's skeletal structure, such as from the individual's heel toward the individual's skull. The mechanical energy transferred into the heel of the wearer, such as during the cycle of a walking gait, while running, or when dismounting an animal, may be uncomfortable or even injurious to the wearer. The transferred mechanical energy may be greatest during high-magnitude impacts, such as after jumping or dismounting from an animal or other object. Thus, there exists a need for heel dampening systems and footwear including the same.